1. Field of the Invention
This invention relates to the formation of amine-containing polymers and polymerizable monomers functionalized with fullerenes to provide polymers with high temperature stability, and monomers capable of forming polymers having high temperature stability.
2. Description of the Related Art
Recently it was discovered that all-carbon molecules, which are soluble in a number of organic solvents, could be produced by the evaporation of graphite. The most common of these all-carbon molecules is a C.sub.60 carbon molecule having the general shape of a geodesic dome, giving rise to its name Buckminsterfullerene after the designer of such geodesic domes. Subsequently it was discovered that a number of such all-carbon molecules existed, having various numbers of carbon atoms and various cage-like shapes, including distorted spheres and even tubular-like shapes.
Fullerene formation and recovery methods are described, for example, by Kratschmer et al. in "Solid C.sub.60 :A New Form of Carbon", published in Nature, Volume 247, pp 354-357, on Sep. 27, 1990; and by Y. K. Bae et al. in "Production, Characterization, and Deposition of Carbon Clusters", prepared for the Symposium on Clusters and Cluster Assembled Materials Special Session on Buckminsterfullerenes, in Boston, Mass. Nov. 29, 1990, and published in The Proceedings of the 1990 Meeting of the MRS Society.
Reaction of such fullerene compounds with other organic moieties has been reported. Hawkins et al., in articles respectively entitled "Organic Chemistry of C.sub.60 (Buckminsterfullerene): Chromatography and Osmylation", J. Org. Chem. 1990, 55, pp 6250-6252 and "Crystal Structure of Osmylated C.sub.60 : Confirmation of the Soccer Ball Framework", Science, Vol. 252, Apr. 1991, pp 312-313, report on a reaction between C.sub.60 fullerene and osmium tetraoxide in the presence of pyridine to form an osmate ester of the fullerene and also report on the crystal structure of the resulting fullerene. The authors also reported, in one of the article, the detection of the presence of a diolatodioxobis(amine)osmium(VI) ester moiety in the product.
The reaction of primary and secondary amines with fullerenes was reported by Wudl et al. in a paper entitled "Survey of Chemical Reactivity of C.sub.60, Electrophile and Dieno-polarophile Par Excellence" presented at an ACS symposium on Apr. 14-19, 1991 and later published in 1992 by the American Chemical Society in their ACS Symposium Series entitled "Fullerenes, Synthesis, Properties, and Chemistry of Large Carbon Clusters" as Chapter 11. Reactions of n-propylamine, dodecylamine, t-butylamine, ethylenediamine, and morpholine with C.sub.60 fullerenes are specifically discussed.